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Halloween trick and treat
Years age my girlfriend won a bet and she got to pick my costume. She knew I enjoyed wearing lingerie. She told me I had to be a female for Halloween. She had her sister bring over some dresses and heels for me. I had to shower, and remove all body hair. Then I put on bra, panties and a garter. They put a wig on me and painted my finger, and toe nails. Put on dangly earrings, and proceeded to apply my makeup. When they were happy with my makeup I got to see myself in a mirror. They had me in thick makeup and RED lipstick. I looked like a hooker in my short dress. We went out to a costume contest, I didn't win but I was got drunk and very horney. Then they drove me to a adult theater and made me go in. I had to stay for an hour because they were leaving me there and they would be back in an hour. I went in got a seat close to the back and quickly the guys came around. Two guys sat on both sides of me. One started touching my leg while he rubbed his dick. They both took their dicks out playing with them. Knowing I might get it over quickly I started stroking them. When they were good and hard I agreed to join them in a booth for privacy. We got in and while I started sucking one guy the other guy pulled my panties down. I was enjoying myself. Cock in my mouth and ass at the same time. They fucked me good giving me their sweet cum. To my surprise when we started to leave the booth two other guys were waiting for their turn. I don't remember how many guys came in me that night. My girlfriend finally found me and led me out. By the time we got home my panties were soaked. After that night she would dress me up and take me to the theater when she wanted to go out. I never complained about getting my stomach and ass pumped full of cum. If I knew I would be there for hours I would just let the guys have me in the main theater. They would line up to have their way with me.
When I w3as 19 I did the same thing I went to an adult theater and before I left I had nine men's cum in my ass. Just about every Friday night it was the same thing over and over then I started in going to one guys house for private shows and believe me that's when I got my fill.
At 17 I was invited to a Halloween party. My older sister convinced me to go saying she would help me with a costume, late that afternoon when I got home from school she had everything laid out. I was going as a hooker. She did my make up and had me dress in one of her sluttiest outfits.
When I got to the party no one knew it was me . As the night went on one of the guys I was on the swim team with started hitting on me. Despite having him grab my ass a few times and trying to kiss me most of the night I avoided him. Finally I had to use the bathroom and as I opened the door to come out he pushed his way in . He had me pushed against the wall trying to kiss me, and drunkenly said he wanted to fuck me. Up till now it was funny but I panicked and said , " dude its me Jerry"! it didn't even register with him , he just kept saying come on baby let me fuck you. Again panicking I told him I was having my period he is like oh ok then. We walk out of the bathroom heading down the hall. He grabs my arm pulls me into the bedroom kisses me right on the lips , tongue in my mouth both hands under my skirt groping my ass.
I tell him again Matt ,Its me Jerry ! let me go. Again either just being drunk or that horny he starts saying "its ok baby I won't tell Jerry, how about just a blowjob?" Its been twenty years and I still don't know why but I sank down to my knees and sucked his cock. The whole time he kept telling me how lucky he was meeting a girl like me at the party .
A few days later Matt was at my house telling me I missed a great party and about this girl that sucked him off in one of the bedrooms. He has no idea to this day that I sucked his cock and choked down his load that night.
Did you ever dress up and suck his cock again? Have you dressed up any more? Did you thank your sister?
I never sucked Matt's cock again and only ever dressed up again about 5 years after I got married.My wife new the story and when she was invited to a new coworker's Halloween party she jumped at the chance to dress me up like a slut. Back in high school and on the swim team I would shave my legs ,but it had been a long time since I had done it. My wife loved feeling my smooth legs and told me I really was passable as a woman.
We go to the party and my wife introduces me as her cousin saying her husband couldn't make the party. As the night went on everyone was drinking and having fun . My wife and I had gotten separated a few times throughout the night , at one point she came walking over with two guys telling me they wanted to go out and smoke a joint with us. My wife was letting the one guy get pretty friendly with her , he was standing behind her rubbing her ass.
We go out to their car and smoke the joint next thing I know my wife is kissing the one guy and the other moved in on me. I stopped him saying I was married. My wife chimed in Its just a kiss your husband will never know. I knew then she wanted to see. We stood outside the car and I kissed him with them making out next to us. Eventually I hear the guy I'm with ask if he can get what his friend is getting . There was my wife stroking his friend's cock. Long story short I sucked him off in front of my wife while his friend fucked her.